2-(Dimethylamino)imidazole | 57166-47-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(Dimethylamino)imidazole
• 英文别名: 1H-Imidazol-2-amine, N,N-dimethyl-；N,N-dimethyl-1H-imidazol-2-amine
• CAS: 57166-47-9
• 化学式: C₅H₉N₃
• mdl: MFCD19218606
• 分子量: 111.147
• InChiKey: WLFOHIVICZSIKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Dimethylamino)imidazole 、 diethyl 1,2,4-triazine-3,5-dicarboxylate 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以84%的产率得到diethyl 2-(dimethylamino)-3H-imidazo[4,5-c]pyridine-4,6-dicarboxylate
  参考文献：
  名称：

  咪唑在反电子需求Diels-Alder反应中的亲液性。4.与1,2,4-三嗪的分子间反应。

  摘要：

  2-取代的咪唑与各种1,2,4-三嗪的分子间逆电子需求环加成反应既产生了咪唑并[4,5-c]吡啶（3-deazapurines），也产生了吡啶并[3,2-d]嘧啶-4-酮（ 8-脱氮庚啶）。产物分布由反应物取代基控制，并受反应温度影响。还开发了一种区域选择性的方法来制备6-未取代的1,2,4-三嗪。通过使用该途径制备8-脱氮庚啶，制备了新的8-脱氮叶酸酯类似物。

  DOI：

  10.1021/jo030049y
• 作为产物：
  描述：

  N'-Benzyl-N''-(2,2-dimethoxy-ethyl)-N,N-dimethyl-guanidine; hydriodide 在 palladium on activated charcoal 盐酸 、 甲酸铵 作用下， 生成 2-(Dimethylamino)imidazole
  参考文献：
  名称：

  Synthesis of 2-dimethylaminoimidazole derivatives: a new access to indolyl-imidazole alkaloids of marine origin.

  摘要：

  The first preparation of 2-dimethylaminoimidazole 1a, a structural feature of several marine products was undertaken and its reactivity investigated. The synthesis of natural alkaloids 5 and 12b was achieved by direct coupling of the easily accessible oxidized 2-dimethylaminoimidazoles 7 and 8 with indole-3-carboxaldehyde and indole respectively, demonstrating the usefulness of this approach for other structurally related natural products.

  DOI：

  10.1016/s0040-4039(00)92376-1

文献信息

• Total synthesis of grossularines-1 and -2
  作者：Tominari Choshi、Shiho Yamada、Eiichi Sugino、Takeshi Kuwada、Satoshi Hibino

  DOI：10.1021/jo00123a028

  日期：1995.9

  The first total syntheses of grossularines-1 (1a) and -2 (1b) have been completed. The cross-coupling reaction between ethyl 3-iodoindole-2-carboxylate (6) and the directed metalation-derived imidazole 9b gave the ethyl 3-(5-imidazolyl)indole-2-carboxylate 11b. Hydrolysis of the ester group of 11b, followed by Curtius rearrangement, yielded the 2-isocyanatoindole 13b. The thermal electrocyclic reaction of 13b was carried out to provide the desired tetracyclic pyrido[2,3-b]indole ring system 14b, which was converted into the triflate 15b. The three-component cross-coupling reaction of the triflate 15b, carbon monoxide, and p-(OMOM)phenylboronic acid (17) followed by hydrolysis gave grossularine-2 (1b) in low yield. In addition, the palladium-catalyzed carbonylation of the triflate 15b afforded the N-deprotected methyl ester 19a or the methyl ester 19b depending on the amounts of triethylamine used. Compound 19a was treated with either p-(OMOM)phenyllithium or 3-(N-TIPS)indolyllithium to obtain grossularine-2 (1b) and grossularine-1 (1a) (37%), respectively. By contrast, when 19b was treated with the same aryllithium reagents, grossularine-2 (1b) (51%) and grossularine-1 (1a) (63%) were produced, respectively.
• Dienophilicity of Imidazole in Inverse Electron Demand Diels−Alder Reactions. 4. Intermolecular Reactions with 1,2,4-Triazines
  作者：Brian R. Lahue、Zhao-Kui Wan、John K. Snyder

  DOI：10.1021/jo030049y

  日期：2003.5.1

  cycloadditions of 2-substituted imidazoles with various 1,2,4-triazines produced both imidazo[4,5-c]pyridines (3-deazapurines) and pyrido[3,2-d]pyrimid-4-ones (8-deazapteridines). The product distribution was controlled by reactant substituents and influenced by reaction temperature. A regioselective method for the preparation of 6-unsubstituted 1,2,4-triazines was also developed. By using this route to 8-deazapteridines

  2-取代的咪唑与各种1,2,4-三嗪的分子间逆电子需求环加成反应既产生了咪唑并[4,5-c]吡啶（3-deazapurines），也产生了吡啶并[3,2-d]嘧啶-4-酮（ 8-脱氮庚啶）。产物分布由反应物取代基控制，并受反应温度影响。还开发了一种区域选择性的方法来制备6-未取代的1,2,4-三嗪。通过使用该途径制备8-脱氮庚啶，制备了新的8-脱氮叶酸酯类似物。
• Synthesis of 2-dimethylaminoimidazole derivatives: a new access to indolyl-imidazole alkaloids of marine origin.
  作者：Angeliki Dalkafouki、Janick Ardisson、Nicole Kunesch、Liliane Lacombe、Jacques E. Poisson

  DOI：10.1016/s0040-4039(00)92376-1

  日期：1991.9

  The first preparation of 2-dimethylaminoimidazole 1a, a structural feature of several marine products was undertaken and its reactivity investigated. The synthesis of natural alkaloids 5 and 12b was achieved by direct coupling of the easily accessible oxidized 2-dimethylaminoimidazoles 7 and 8 with indole-3-carboxaldehyde and indole respectively, demonstrating the usefulness of this approach for other structurally related natural products.